2089 Winningway St · Port Charlotte, FL 33948

$235,000

4 bd · 2.0 ba · 1,348 sqft · SingleFamily public records · 18 Days on market

Built 1989 9,999 sqft lot Est $252k · 7% under

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Why this score? — see what drove the D+ grade

The composite is a weighted blend of 9 inputs, each scored 0–100. Each bar is that input's sub-score; the figure is the points it added to the 100-point composite (weight × sub-score).

• Cash flow +14.9/30.0
• ARV discount +10.5/15.0
• 1% rule +4.6/10.0
• Schools +4.6/10.0
• DSCR +4.5/10.0
• Livability +3.2/5.0
• Condition / age +2.5/5.0
• Rent growth +2.1/5.0
• Appreciation +0.0/10.0

Listing remarks MLS

PLEASANT TO SHOW WITH EXTRA LAND! Well maintained home with chair rails, French doors, 4 skylights, cathedral ceiling, 16-inchfloor tile, tray ceiling w/ lights in kitchen. Built-in linen organizer in master closet. Dimmer light in dining room, double switch in garage area & lanai. Solid wood kitchen cabinets, 6 ceiling fans. .. and the list goes on. ! Seller currently converted garage to a temporary 3rd bedroom tastefully done, creating 1720 living sq ft under air, designed to be converted back to it's original 2 car garage, based on owner's preference or need. 2 CONTIGOUS LOTS have been made into park like setting with abundant palm trees giving a real "show off" appearance. . Home warranty from seller to buyer as well.

Key facts

• Storage room
• New water heater
• New ac

Tags

• NEW AC
• NEW ROOF
• NEW WATER HEATER
• INSIDE LAUNDRY ROOM
• STORAGE ROOM

Property features AI

Finance

• Other: Residential, RSF3.5 zoning
• HOA & community: No association indicated

Exterior

• Parking: Converted garage; Driveway
• Utilities: Public water; Septic tank; Cable available; Electricity connected; Water connected
• Home design: Single family residence; One story; East facing
• Construction: Block and stucco construction; Shingle roof; Slab foundation; Built on a lot of approximately 0.23 acres
• Exterior features: Enclosed patio/porch; Hurricane shutters; Paved lot; Irrigation equipment

Interior

• Kitchen: Dishwasher; Range; Microwave; Electric water heater
• Bedrooms: 3 bedrooms
• Flooring: Carpet; Ceramic tile
• Bathrooms: 2 full bathrooms
• Heating & cooling: Central heating (electric); Central air conditioning
• Interior features: Cathedral ceilings; Tray ceilings; Ceiling fans; Open floorplan; Kitchen/family room combo; Walk-in closets; Skylight(s)
• Laundry & utility: Inside laundry room; Washer; Dryer; Inside utility room

What this means for you Summary

Snapshot

• This is a 4-bed/2.0-bath single-family listed at $235k.

Deal economics

• At list price, monthly cash flow is $67 ($803/yr) — positive.
• The deal already cash-flows at list — no discount required.
• To meet the 1% rule (rent ≥ 1% of price), the offer needs to be $226k (3.9% below list).
• Recommended offer: $226k (3.9% below list) — sets the bar for 1% rule.
• Cap rate 6.6% vs local median 4.4% in Port Charlotte — top-decile yield for the area; either an underpriced asset or a hidden risk that comps aren't pricing in. Stress-test before assuming the spread holds.

Location & tenants

• Location reads 65/100 on livability (#655 in FL) — a middle-class / working-renter tenant base. Strengths: cost of living A+, housing A+; Watch: employment D, amenities F, commute F.
• Charlotte (suburban): math 54% / reading 54% proficiency, ranked #22 of 73 in FL (top 30%) — acceptable for families but not a draw, mixed tenant base, ~2y average lease.
• Zoned schools: Liberty Elementary School (math 56% / reading 56%, grade C+, #832 of 2,144 statewide, top 40%, 622 students, 56% FRL); Port Charlotte High School (math 23% / reading 38%, grade F, #434 of 667 statewide, top 66%, 1,649 students, 43% FRL) — zoned schools at 50% FRL track the district average.
• Market conditions: Rents soft (-1.6%/yr); 953 active listings in the ZIP; 18 comparable units currently listed for rent nearby; rentals at typical pace (median 22d on market — plan ~3-4 weeks tenant-placement turnaround); 4,585 units permitted in Charlotte County in 2024 (703 in 5+ unit buildings).
• This rent runs 43% of the median local income ($63k/yr) — at the standard rent-burdened threshold; future hikes will face affordability resistance.

Forward outlook

• Local home prices are declining (-3.0%/yr); year-one equity from $2k of loan paydown is wiped out by about $7k of value loss. Plan a longer hold.
• Charlotte County population projected at +24% by 2050 — long-run rental-demand tailwind backs the buy-and-hold thesis.

Negotiation context

• It's been on market 18 days — a 2% lower offer ($231k) is reasonable based on typical stale-listing flexibility.
• 3 sale attempts since 11y ago with the ask held roughly flat each time — persistent listings suggest the price (not the market) is what's stuck; bring a comps-based counter.
• Current owner paid $140k; list at $235k implies a 68% gain — meaningful room to come down on a strong offer.

Risks & watch-outs

• Climate carrying-cost: major flood risk; severe wind risk, 99% chance of damaging wind over 30y; extreme-heat days projected 6→24/yr by 2055 (HVAC capex compounding) — expect insurance premiums to compound above CPI over the hold.

Recommended offer $225,773 (3.9% below list)

Questions for the listing agent

1. Is there a deadline driving the sale (1031 exchange, divorce, estate, relocation)? That informs how much negotiation room exists.
2. Schools are D-rated, which usually means shorter tenancies and higher turnover. Who's the typical renter profile here, and what's been the actual vacancy rate?
3. The area grade is low — what's the realistic commute time and amenity access for the typical tenant pool here? Any planned neighborhood developments (good or bad) we should know about?
4. What's the average days-on-market for RENTAL listings here right now (not sales)? A rising rental-DOM trend means longer vacancies and softer asking-rent achievability than the comps imply.
5. What's the recent tenant-quality profile in this submarket — average credit score on applications, eviction rate, late-payment / NSF rate, and stable-employment percentage? A property-management company in the area should have these aggregated.
6. How much new for-sale + rental construction is in the pipeline within 1–3 miles? Heavy new supply typically softens prices + rents 12–24 months out; constrained supply supports both.

Investment metrics

• 1% rule: 0.96% ✗
• Cap rate: 6.63%
• Cash-on-cash: 1.22%
• DSCR: 1.05
• GRM: 8.7

CMA / ARV

• ARV (on-the-fly): $252,076
• Comps found: 8

Show comp detail 8 sales within ~0.75 mi

Address	Dist	Beds/Ba	Sqft	Sold	Price	$/sf	Match
18159 Summerdown Ave	0.28mi	3/2.0 (-1)	1,408 (+4%)	7mo	$320,000	$227	68
2106 Wonderwin St	0.09mi	3/2.0 (-1)	1,430 (+6%)	19mo	$238,000	$166	64
18275 Cortland Ave	0.25mi	3/2.0 (-1)	1,273 (-6%)	22mo	$170,000	$134	56
2293 Summit St	0.42mi	3/2.0 (-1)	1,456 (+8%)	9mo	$325,000	$223	54
17505 Harris Ave	0.41mi	4/2.0	1,456 (+8%)	18mo	$205,000	$141	53
2341 Granadeer St	0.58mi	3/2.0 (-1)	1,183 (-12%)	5mo	$223,000	$189	43
18248 Regan Ave	0.74mi	3/2.0 (-1)	1,480 (+10%)	4mo	$216,000	$146	41
18139 Regan Ave	0.75mi	4/2.0	1,499 (+11%)	10mo	$280,000	$187	38

Match score weights: distance 35% · size 25% · config 20% · recency 20%. Top-matched comps best support the ARV.

Projected returns pro-forma

-3.0% appreciation · 0.0% rent growth · sell at horizon

5-year hold

• IRR: -17.9%
• Equity multiple: 0.39×
• Total profit: $-40,344
• Equity at exit: $35,039

10-year hold

• IRR: -17.8%
• Equity multiple: 0.17×
• Total profit: $-54,844
• Equity at exit: $20,319

Cash invested: $65,800 (down + closing). Projections, not guarantees.

Landlord ↔ Tenant lean methodology

• Overall (STATE): 87 Strongly Landlord-Friendly
• State Florida: 87 Strongly Landlord-Friendly · R+3
• County: — inherits STATE
• City: — inherits STATE

3-day pay-or-quit; preempts local rent control; landlord-friendly statutes. Court speed varies by county.

Methodology + full state rankings →

ZIP-level market 33948

• Home prices YoY: -14.9%
• Rents YoY: -1.6%
• Active inventory: 953
• Price-to-rent: 8.7×

Monthly cashflow live

• Estimated rent: $2,258 high
• Mortgage (P&I): −$1,232
• Tax from tax record: −$386 /mo · $4,637/yr
• Insurance: −$98
• HOA: −$0
• Vacancy / Maint / Mgmt: −$474
• Net cashflow: $67

Break-even live

Break-even rent $2,173

Max offer price $235,000

Occupancy floor 92%

UW: 25.0% down · 7.5% · 30yr · 1.5% tax · 5.0% vac · 8.0% maint · 8.0% mgmt

Financing live

Cash to close

• Down payment: $58,750
• Closing costs: $7,050
• Reserves months: —
• Total cash needed: —

Rent comps 18 comps

Address	Beds	Baths	Sqft	Rent	$/sqft	DOM	Units	Dist
2223 Tinker St Port Charlotte, FL	3.0	2.0	1337	$2,400	$1.80	21d	1	0.50mi
2144 Pellam Blvd Port Charlotte, FL	4.0	2.5	1751	$2,106	$1.20	14d	1	0.69mi
2457 Haven St Port Charlotte, FL	3.0	2.0	1150	$1,775	$1.54	21d	1	0.73mi
17319 Terry Ave Port Charlotte, FL	3.0	2.0	1478	$2,095	$1.42	21d	1	0.77mi
1275 Price Cir NW Port Charlotte, FL	3.0	2.0	1810	$1,700	$0.94	21d	1	0.77mi
2113 Como St Port Charlotte, FL	3.0	2.0	1162	$1,500	$1.29	21d	1	0.87mi
2022 Dorion St Port Charlotte, FL	3.0	2.0	1200	$1,695	$1.41	14d	1	0.97mi
17107 Thompson Ave Unit 17107 Port Charlotte, FL	3.0	2.0	1190	$1,900	$1.60	21d	1	1.11mi
3153 Jody St Port Charlotte, FL	4.0	2.0	1650	$1,945	$1.18	21d	1	1.20mi
1011 Tropical Ave NW Port Charlotte, FL	3.0	2.0	1558	$1,950	$1.25	21d	1	1.22mi
2225 Fraser St Port Charlotte, FL	3.0	2.0	1600	$2,500	$1.56	14d	1	1.24mi
2233 Fraser St Unit 2235 Port Charlotte, FL	3.0	2.0	1162	$1,647	$1.42	21d	1	1.24mi
17051 Greenan Ave Port Charlotte, FL	4.0	2.0	1833	$1,995	$1.09	14d	1	1.29mi
18423 Elgin Ave Port Charlotte, FL	4.0	2.0	1636	$2,200	$1.34	21d	1	1.29mi
1000 Chevy Chase St Port Charlotte, FL	3.0	2.0	1589	$3,500	$2.20	21d	1	1.30mi
1225 Armsdale Ave Port Charlotte, FL	3.0	2.0	1140	$1,525	$1.34	21d	1	1.34mi
945 Chevy Chase St Port Charlotte, FL	3.0	2.0	1582	$2,875	$1.82	21d	1	1.38mi
17424 Poston Ave Port Charlotte, FL	4.0	2.0	1833	$1,925	$1.05	14d	1	1.38mi

Listing history 15 events

1. 2026-06-18
   days on market $235,000 Active 18 DOM
2. 2026-06-17
   days on market $235,000 Active 17 DOM
3. 2026-06-16
   days on market $235,000 Active 16 DOM
4. 2026-06-15
   pricestatus $235,000 Active 15 DOM
5. 2026-04-24
   status Pending
6. 2026-04-09
   listed $232,800 Active
7. 2024-08-21
   historical $1,750
8. 2024-08-07
   price $1,750
9. 2024-07-19
   price $1,800
10. 2024-07-04
    listed $1,900
11. 2015-08-03
    soldstatus $140,000
12. 2015-07-31
    soldstatus $140,000 Sold 752-char remark

    Show marketing remark (752 chars)

    PLEASANT TO SHOW WITH EXTRA LAND! Well maintained home with chair rails, French doors, 4 skylights, cathedral ceiling, 16-inchfloor tile, tray ceiling w/ lights in kitchen. Built-in linen organizer in master closet. Dimmer light in dining room, double switch in garage area & lanai. Solid wood kitchen cabinets, 6 ceiling fans. .. and the list goes on. ! Seller currently converted garage to a temporary 3rd bedroom tastefully done, creating 1720 living sq ft under air, designed to be converted back to it's original 2 car garage, based on owner's preference or need. 2 CONTIGOUS LOTS have been made into park like setting with abundant palm trees giving a real "show off" appearance. . Home warranty from seller to buyer as well.

13. 2015-06-27
    status Pending 752-char remark

    Show marketing remark (752 chars)

    PLEASANT TO SHOW WITH EXTRA LAND! Well maintained home with chair rails, French doors, 4 skylights, cathedral ceiling, 16-inchfloor tile, tray ceiling w/ lights in kitchen. Built-in linen organizer in master closet. Dimmer light in dining room, double switch in garage area & lanai. Solid wood kitchen cabinets, 6 ceiling fans. .. and the list goes on. ! Seller currently converted garage to a temporary 3rd bedroom tastefully done, creating 1720 living sq ft under air, designed to be converted back to it's original 2 car garage, based on owner's preference or need. 2 CONTIGOUS LOTS have been made into park like setting with abundant palm trees giving a real "show off" appearance. . Home warranty from seller to buyer as well.

14. 2015-06-24
    listed $139,850 Active 752-char remark

    Show marketing remark (752 chars)

    PLEASANT TO SHOW WITH EXTRA LAND! Well maintained home with chair rails, French doors, 4 skylights, cathedral ceiling, 16-inchfloor tile, tray ceiling w/ lights in kitchen. Built-in linen organizer in master closet. Dimmer light in dining room, double switch in garage area & lanai. Solid wood kitchen cabinets, 6 ceiling fans. .. and the list goes on. ! Seller currently converted garage to a temporary 3rd bedroom tastefully done, creating 1720 living sq ft under air, designed to be converted back to it's original 2 car garage, based on owner's preference or need. 2 CONTIGOUS LOTS have been made into park like setting with abundant palm trees giving a real "show off" appearance. . Home warranty from seller to buyer as well.

15. 2002-09-09
    soldstatus $92,500

ⓘ Source: listings_history table (triggers on properties + properties_extension) + one-shot backfill from property_details.listing_events for pre-trigger history.

Tax reassessment forecast FL · Resets to sale price

• Current annual tax: $4,637 · $386/mo
• Projected year-2 tax: $4,637 · $386/mo
• Expected delta: $0/yr ($0/mo · 0.0%)

ⓘ Screening estimate from a state-policy table — verify with the county assessor before closing.

Climate risk First Street

• 🌊 Flood 6/10 Major FEMA zone X (shaded) · 57% chance over 30 yrs
• 🔥 Wildfire 1/10 Low
• 🌡 Heat 10/10 Extreme 6 d/yr ≥107°F today · 24 d/yr by 30 yrs out
• 💨 Wind 10/10 Extreme 99% chance of damaging wind over 30 yrs
• 🫁 Air quality 3/10 Moderate 2 unhealthy d/yr today · 3 by 30 yrs out

Taxation est. · year 1

• Rental income: $27,093
• − Mortgage interest: −$13,164
• − Property taxes: −$4,637
• − Insurance: −$1,175
• − Repairs & maintenance: −$2,167
• − Management: −$2,167
• − Depreciation: −$6,836
• Taxable loss: −$3,054
• Est. tax savings @ 24.0%: +$733
• After-tax cash flow: $1,536/yr

For passive investors: Depreciation is non-cash, so a rental often shows a tax loss while cash-flowing — sheltering income. Rental losses are passive: they offset passive income freely, and up to $25,000/yr can offset ordinary (W-2) income if you actively participate and your MAGI is under $100k (phasing out to $0 by $150k); unused losses carry forward. On sale, claimed depreciation is recaptured at up to 25%, and gains may owe capital-gains tax (a 1031 exchange can defer both). Figures are a year-1 estimate at your 24.0% rate — not tax advice; consult a CPA.

Schools (NCES district)

• District: Charlotte
• NCES district ID: 1200240
• Math proficiency: 54% ▼ -6.00%
• Reading proficiency: 54% ▼ -1.00%
• Median HH income: $44,864
• Composite: 45.62/100
• National rank: #2586
• State rank: #22 of 73 in FL

Livability — Port Charlotte

• Score: 65/100
• State rank: #655
• US rank: #13081

Category grades

Amenities F Commute F Cost of living A+ Crime C+ Employment D Housing A+ Health & safety D- User ratings D+

Schools grade is shown separately in the Schools card above.

Census & demographics

• Census place: Port Charlotte, FL
• County: Charlotte County · 196,994 people
• City population: 102,180
• Metro: Punta Gorda, FL
• Population (ZIP): 18,696
• Household income: $62,744
• Rent vs Own: 13.8% rent · 86.2% own
• Severe rent burden: 501.0

Population outlook (Charlotte County) Hauer SSP2

• Today (2025): 198,646 people
• By 2030: 210,507 · +6.0%
• By 2040: 230,857 · +16.2%
• By 2050: 247,148 · +24.4%
• By 2075: 281,777 · +41.8%
• By 2100: 293,609 · +47.8%

Race, ethnicity, and origin ACS 2023

• Neighborhood character: Predominantly White (79%)
• Race & ethnicity: White 79% Two or more races 8% Black 7% Hispanic / Latino 7% Asian 2%
• Hispanic origin (detail): Mexican 2% Puerto Rican 1%
• Common ancestry: Lithuanian 5% Romanian 4% Iranian 2%
• Foreign-born: 11% · Canada
• Languages at home: 88% English-only · Spanish 5% Russian/Polish/Slavic 2% Other Indo-European 1%

Political lean MEDSL · Charlotte

• 2024 margin: Solid R (+34.0) · D 32.7% · R 66.7%
• 2008→2024 swing: -26.7pp toward R · 2008: -7.2pp · 2024: -34.0pp
• All cycles: 2024: R+34.0 2020: R+26.6 2016: R+27.8 2012: R+14.3 2008: R+7.2

Not yet ingested

• Civics: —

Market trends

• HPI YoY: ▼ -55.31%
• Current HPI: 315.0548
• Rent YoY: ▼ -1.63%
• Metro: Punta Gorda, FL
• State GDP YoY: ▲ 3.28%
• F500 in state: 36

Industry mix (Fortune 500 HQ in FL)

Industry	F500 HQs	Revenue
▸Industrial Technology	2	$29B
▸Insurance	2	$17B
▸Retail	1	$60B
▸Technology Distribution	1	$58B
▸Homebuilding	1	$35B
▸Technology Manufacturing	1	$35B

Price history

+151.7% since first listed

11 events — show timeline

• 2026-04-24 Pending — Stellar MLS as Distributed by MLS Grid
• 2026-04-09 Listed $232,800 Stellar MLS as Distributed by MLS Grid
• 2024-08-21 Rental Removed $1,750 STELLARMLS
• 2024-08-07 Price Changed $1,750 STELLARMLS
• 2024-07-19 Price Changed $1,800 STELLARMLS
• 2024-07-04 Listed for Rent $1,900 STELLARMLS
• 2015-08-03 Sold (Public Records) $140,000 Public Records
• 2015-07-31 Sold (MLS) $140,000 Stellar MLS as Distributed by MLS Grid
• 2015-06-27 Pending — Stellar MLS as Distributed by MLS Grid
• 2015-06-24 Listed $139,850 Stellar MLS as Distributed by MLS Grid
• 2002-09-09 Sold (Public Records) $92,500 Public Records

Property tax history

+8.8%/yr

Latest (2025): $4,637 · +4.5% YoY. Source: county tax records.